The Center for Sales Strategy Blog

The Loneliness of Sales Leadership

Let’s be honest, leadership can be lonely.

If you’re a senior sales leader, your days are filled with decisions that impact revenue, people, and strategy. You’re expected to have answers, keep morale high, and deliver results quarter after quarter. But who do you turn to for advice, perspective, or a sounding board?

Too often, sales leaders find themselves leading in isolation relying solely on their own experiences or the limited perspectives within their organization. Over time, this can quietly erode growth, confidence, and clarity.

Securing appointments has always been a sales challenge, but in media sales today, it’s reached a breaking point. The  6th Annual Media Sales Report shows that booking meetings, advancing deals, and closing business require more persistence, better tools, and sharper strategies than ever before.

Here’s what the data from the Setting Appointments & Sales Process section tells us—and what sales leaders must do now to keep their pipelines full.

In this episode, we’re taking a closer look at how executive coaching helps leaders evolve so their teams can truly thrive. 

And joining Matt is Donna Hall, SVP/General Manager at Robertson Lowstuter, whose piece in the 2025 Talent Magazine explores how executive coaching creates a ripple effect across teams and culture.

Whether you’re new to leadership or deep into your career, this conversation will help you rethink what great executive development looks like.

Donna shares such rich insights, like: 

• How, if you want to be the best leader you can be, it takes the recognition that everyone has areas for growth 
• Why the cornerstone of great leadership begins with authenticity 
• And, finally, how Michael Jordan didn’t have a coach because he was weak. He had a coach because he was committed to staying at the top of his game

Sales enablement should be the bridge between your sales team and closed deals—but in many media organizations, that bridge has cracks. The 6th Annual Media Sales Report reveals that while most sellers have access to some resources, too many are questioning their quality, effectiveness, and the strategy behind them.

Here’s what the Sales Enablement data tells us—and what media sales leaders need to do to make it a true revenue driver.

In media sales, top talent is developed, not found.

The 6th Annual Media Sales Report reveals a consistent theme across high-performing teams: intentional learning and development. But while salespeople crave growth, most organizations still struggle to deliver it consistently.

Here’s what the data from the Learning & Development section of the report tells us, and what sales leaders must do to bridge the performance gap.

Effective communication is the cornerstone of success. As sales leaders, it's imperative to ensure your team masters the art of communication. The 7 Cs—Clear, Concise, Concrete, Correct, Coherent, Complete, and Courteous—are not just principles; they are the bedrock of every successful sales interaction. 

Salespeople must be adept at conveying their messages in a way that resonates with prospects and clients. The ability to communicate effectively can make the difference between closing a deal and losing a potential customer. By mastering the 7 Cs, your team can enhance their communication skills, build stronger relationships, and drive better results. 

Let's dive into how you can instill these essential communication skills in your sales team. 

Sales managers, let’s talk about the lifeblood of your team’s success—your sales funnel. If it’s weak, your sales will be inconsistent. If it’s strong, your team will have a steady stream of deals to close. Your job? Make sure it’s built for success. 

Here’s how you can strengthen your team’s funnel and keep revenue flowing.

As B2B sales leaders and managers, your role in guiding your sales teams to success is more critical than ever. With the ever-evolving sales landscape, it's essential to stay ahead by focusing on key areas that can significantly improve your team's performance. Here are some crucial topics to consider, especially as you work through Q1 to set your team up for success early in the year:

Leadership is a challenging yet vital role in any organization. Great leaders can drive a company to success, while ineffective ones can lead to its downfall. Unfortunately, many companies overlook the importance of training their leaders, expecting them to succeed with little to no preparation. If leadership is so critical, how can organizations ensure their leaders are set up for success? 

I often have conversations with sales managers who lament their teams' lack of accountability, implementation, and follow-through. They talk about struggling to get new initiatives or processes adopted consistently.

In these situations, my typical response is: "Let's talk about your weekly one-on-one meetings and how you use them to drive accountability."

One-on-one meetings between managers and their salespeople are critical for staying aligned, removing blockers, and driving performance. However, many managers fail to run these meetings effectively. Here is a proven guide to great one-on-one meetings that drive real accountability.